Thienylsulphonylamino(thio)carbonyl compounds

ABSTRACT

The invention relates to novel thienylsulphonylamino(thio)carbonyl compounds of the formula (I),                    
     in which 
     Q represents oxygen or sulphur, 
     R 1  represents cyano, halogen or in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, 
     R 2  represents cyano, halogen or in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and 
     R 3  represents in each case optionally substituted heterocyclyl having 5 ring members, at least one of which represents oxygen, sulphur or nitrogen and one to three others may represent nitrogen, 
     and salts of compounds of the formula (I), to processes and novel intermediates for preparing the novel compounds and to their use as herbicides.

This Application is a divisional patent application of U.S. patentapplication Ser. No. 09/319,021 filed Jun. 1, 1999 to Muller et al,which subsequently issued as U.S. Pat. No. 6,383,988 on May 7, 2002,which in turn was the national stage of PCT Application No.PCT/EP97/06560 filed Nov. 24, 1997, which in turn claimed and perfectedits claim of priority of German Patent Application No. 196 50 196.2filed Dec. 4, 1996, priority of which is hereby claimed in the presentApplication.

The invention relates to novel thienylsulphonylamino(thio)carbonylcompounds, to a plurality of processes and novel intermediates for theirpreparation and to their use as herbicides.

It is already known that certain sulphonylaminocarbonyl compounds haveherbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291,EP 507171, EP 534266, DE 4029753). However, the activity of thesecompounds is not in all respects satisfactory.

This invention, accordingly, provides the novelthienylsulphonylamino(thio)-carbonyl compounds of the general formula(I),

in which

Q represents oxygen or sulphur,

R¹ represents cyano, halogen or in each case optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxyor alkinyloxy having in each case up to 6 carbon atoms,

R² represents cyano, halogen or in each case optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxyor alkinyloxy having in each case up to 6 carbon atoms, and

R³ represents in each case optionally substituted heterocyclyl having 5ring members, at least one of which represents oxygen, sulphur ornitrogen and one to three others may represent nitrogen,

and salts of compounds of the formula (I).

The novel thienylsulphonylamino(thio)carbonyl compounds of the generalformula (I) are obtained when

(a) sulphonamides of the general formula (II)

in which

R¹ and R² are each as defined above,

are reacted with (thio)carboxylic acid derivatives of the generalformula (III)

in which

Q and R³ are each as defined above and

Z represents halogen, alkoxy, aryloxy or arylalkoxy,

if appropriate in the presence of an acid acceptor and if appropriate inthe presence of a diluent,

or when

(b) sulphonyl iso(thio)cyanates of the general formula (IV)

in which

Q, R¹ and R² are each as defined above,

are reacted with heterocycles of the general formula (V)

H—R³⁻¹  (V)

in which

R³⁻¹ represents optionally substituted heterocyclyl having 5 ringmembers, at least one of which represents >N—H,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

(c) sulphonyl chlorides of the general formula (VI)

in which

R¹ and R² are each as defined above,

are reacted with heterocycles of the general formula (V)

H—R³⁻¹  (V)

in which

R³⁻¹ is as defined above under (b),

and metal (thio)cyanates of the general formula (VII)

MQCN  (VII)

in which

Q is as defined above and

M represents a metal equivalent,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

(d) sulphonyl chlorides of the general formula (VI)

in which

R¹ and R² are each as defined above,

are reacted with (thio)carboxamides of the general formula (VIII)

in which

Q and R³ are each as defined above under formula (I),

if appropriate in the presence of an acid acceptor and if appropriate inthe presence of a diluent,

or when

(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)

in which

Q, R¹ and R² are each as defined above and

Z represents halogen, alkoxy, aryloxy or arylalkoxy,

are reacted with heterocycles of the general formula (V)

H—R³⁻¹  (V)

in which

R³⁻¹ is as defined above under (b),

if appropriate in the presence of an acid acceptor and if appropriate inthe presence of a diluent,

and the compounds of the formula (I) obtained by the processes (a), (b),(c), (d) or (e) are, if appropriate, converted into salts by customarymethods.

According to their nature, the processes (b), (c) and (e) are onlysuitable for preparing those compounds of the formula (I) in which R³represents R³⁻¹.

The novel thienylsulphonylamino(thio)carbonyl compounds of the generalformula (I) have strong herbicidal activity.

The invention preferably provides compounds of the formula (I) in which

Q represents oxygen or sulphur,

R¹ represents cyano, halogen, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionallycyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, representsoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, orrepresents in each case optionally cyano- or halogen-substitutedC₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy,

R² represents cyano, halogen, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionallycyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, representsoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, orrepresents in each case optionally cyano- or halogen-substitutedC₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy, and

R³ represents in each case optionally substituted heterocyclyl of theformulae below

in which

Q¹, Q² and Q³ each represent oxygen or sulphur and

R⁴ represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents in each case optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy, representsdi-(C₁-C₄-alkyl)-amino, represents in each case optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkylamino or C₃-C₆-cycloalkyl-C₁-C₄-alkyl,or represents in each case optionally fluorine-, chlorine-, bromine-,cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl and/orC₁-C₄-alkoxy-substituted phenyl or phenyl-C₁-C₄-alkyl,

R⁵ represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine,chlorine, bromine, iodine, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents in each case optionally fluorine-,chlorine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedC₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy,C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio,C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, representsdi-(C₁-C₄-alkyl)-amino, represents in each case optionally methyl-and/or ethyl-substituted aziridino, pyrrolidino, piperidino ormorpholino, represents in each case optionally fluorine-, chlorine-,bromine-, cyano -and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio orC₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or represents in each case optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio,phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or

R⁴ and R⁵ together represent optionally branched alkanediyl having 3 to11 carbon atoms, futhermore

R⁶, R⁷ and R⁸ are identical or different and each represent hydrogen,cyano, fluorine, chlorine, bromine, or represent in each case optionallyfluorine-, chlorine-, bromine- or C₁-C₄-alkoxy-substituted alkyl,alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio,alkenylthio, alkinylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms or represent optionally cyano-,fluorine-, chlorine-, bromine or C₁-C₄-alkyl-substituted cycloalkylhaving 3 to 6 carbon atoms.

The invention furthermore preferably provides sodium, potassium,magnesium, calcium ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts ofcompounds of the formula (I) in which Q, R¹, R² and R³ each have themeaning given above as being preferred.

The invention in particular provides compounds of the formula (I) inwhich

Q represents oxygen or sulphur,

R¹ represents cyano, fluorine, chlorine, bromine, represents in eachcase optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, or represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,

R² represents cyano, fluorine, chlorine, bromine, represents in eachcase optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, or represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,and

R³ represents in each case optionally substituted heterocyclyl of theformulae below

in which

Q¹, Q² and Q³ each represent oxygen or sulphur and

R⁴ represents hydrogen, hydroxyl, amino, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted propenyl,butenyl, propinyl or butinyl, represents in each case optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy or butenyloxy, represents dimethylamino or diethylamino,represents in each case optionally fluorine-, chlorine-, methyl- and/orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally fluorine-,chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenylor benzyl

R⁵ represents hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine,bromine, represents in each case optionally fluorine-, chlorine-,cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, represents in each case optionally fluorine-,chlorine- or bromine-substituted ethenyl, propenyl, butenyl, propinyl orbutinyl, represents in each case optionally fluorine-, chlorine-,cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-,i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-,i-, s- or t-butylamino, represents propenyloxy, butenyloxy, propinyloxy,butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio,butinylthio, propenylamino, butenylamino, propinylamino or butinylamino,represents dimethylamino, diethylamino or dipropylamino, represents ineach case optionally fluorine-, chlorine-, methyl- and/orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, methyl-, trifluoromethyl-,methoxy- and/or methoxycarbonyl-substituted phenyl, benzyl, phenoxy,benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or

R⁴ and R⁵ together represent optionally branched alkanediyl having 3 to11 carbon atoms, furthermore

R⁶, R⁷ and R⁸ are identical or different and each represent hydrogen,cyano, fluorine, chlorine, bromine, or represent in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl,butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,propenyloxy, butenyloxy, propinyloxy, butinyloxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio,butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, or represent cyclopropyl.

A very particularly preferred group of compounds according to theinvention are those compounds of the formula (I) in which

Q represents oxygen or sulphur,

R¹ represents methyl, ethyl, n- or i-propyl,

R² represents methyl, ethyl, n- or i-propyl and

R³ represents optionally substituted triazolinyl of the formula below

in which

Q¹ represents oxygen or sulphur and

R⁴ represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, represents in eachcase optionally fluorine- or chlorine-substituted propenyl or propinyl,represents methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n-or i-propylamino, represents propenyloxy, represents dimethylamino orrepresents cyclopropyl,

R⁵ represents chlorine or bromine, represents in each case optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each caseoptionally fluorine-, chlorine- or bromine-substituted ethenyl,propenyl, butenyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio,propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino,butenylamino, propinylamino or butinylamino, represents dimethylamino,diethylamino or dipropylamino, represents in each case optionallyfluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio,cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio,cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino orcyclohexylmethylamino, or represents in each case optionally fluorine-,chlorine-, methyl-, trifluoromethyl-, methoxy- and/ormethoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy,phenylthio, benzylthio, phenylamino or benzylamino, or

R⁴ and R⁵ together represent optionally branched alkanediyl having 3 to11 carbon atoms.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with each otheras desired, that is to say combinations between the stated preferredranges are also possible.

Using, for example, 4-bromo-2-methyl-thiophene-3-sulphonamide and5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-thioneas starting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following equation:

Using, for example, 4-chloro-2-ethyl-3-thienylsulphonyl isothiocyanateand 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as startingmaterials, the course of the reaction in the process (b) according tothe invention can be illustrated by the following equation:

Using, for example, 4-ethyl-2-methoxy-thiophene-3-sulphonyl chloride,5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and potassiumcyanate as starting materials, the course of the reaction in the process(c) according to the invention can be illustrated by the followingequation:

Using for example, 4-cyano-2-isopropyl-thiophene-3-sulphonly chlorideand 5-methyl-1,2,4-oxadiazole-3-carboxamide as starting materials, thecourse of the reaction in the process (d) according to the invention canbe illustrated by the following equation:

Using, for example,N-(4-fluoro-2-trifluoromethyl-thiophen-3-yl-sulphonyl)-O-methyl-urethaneand 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as startingmaterials, the course of the reaction in the process (e) according tothe invention can be illustrated by the following equation:

The formula (II) provides a general definition of the sulphonamides tobe used as starting materials in the process (a) according to theinvention for preparing the compounds of the formula (I). In the formula(II), R¹ and R² each preferably or in particular have those meaningswhich have already been mentioned above, in the description of thecompounds of the formula (I) according to the invention, as beingpreferred or as being particularly preferred for R¹ and R².

The starting materials of the formula (II) have hitherto not beendisclosed in the literature; as novel substances, they also form part ofthe subject-matter of the present application.

The novel sulphonamides of the formula (II) are obtained when sulphonylchlorides of the formula (VI)

in which

R¹ and R² are each as defined above,

are reacted with ammonia, if appropriate in the presence of a diluent,such as, for example, water, at temperatures between 0° C. and 50° C.(cf. the Preparation Examples).

The sulphonyl chlorides of the formula (VI) have likewise hitherto notbeen disclosed in the literature; as novel substances, they also formpart of the subject-matter of the present application.

The novel sulphonyl chlorides of the formula (VI) are obtained whencorresponding amino compounds of the general formula (X)

in which

R¹ and R² are each as defined above,

are reacted with an alkali metal nitrite, such as, for example, sodiumnitrite, in the presence of hydrochloric acid at temperatures between−10° C. and +10° C. and the resulting diazonium salt solution is reactedwith sulphur dioxide in the presence of a diluent, such as, for example,dichloromethane, 1,2-dichloroethane or acetic acid, and in the presenceof a catalyst, such as, for example, copper(I) chloride and/orcopper(II) chloride, at temperatures between −10° C. and +50° C. (cf.the Preparation Examples).

The amino compounds of the formula (X) required as precursors are knownand/or can be prepared by processes known per se (cf. DE 33 03 388).

The formula (III) provides a general definition of the (thio)carboxylicacid derivatives further to be used as starting materials in the process(a) according to the invention for preparing the compounds of theformula (I). In the formula (III), Q and R³ each preferably or inparticular have that meaning which has already been mentioned above, inthe description of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for Qand R³; Z preferably represents fluorine, chlorine, bromine,C₁-C₄-alkoxy, phenoxy or benzyloxy, in particular represents chlorine,methoxy, ethoxy or phenoxy.

The starting materials of the formula (III) are known and/or can beprepared by processes known per se (cf. EP 459244, EP 341489, EP 422469,EP 425948, EP 431291, EP 507171, EP 534266).

The formula (IV) provides a general definition of the sulphonyliso(thio)cyanates to be used as starting materials in the process (b)according to the invention for preparing the compounds of the formula(I). In the formula (IV), Q, R¹ and R² each preferably or in particularhave that meaning which has already been mentioned above, in thedescription of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for Q,R¹ and R².

The sulphonyl iso(thio)cyanates of the formula (IV) have hitherto notbeen disclosed in the literature; as novel substances, they also formpart of the subject-matter of the present application.

The novel sulphonyl iso(thio)cyanates of the formula (IV) are obtainedwhen sulphonamides of the general formula (II)—above—are reacted withphosgene and thiophosgene, respectively, if appropriate in the presenceof an alkyl isocyanate, such as, for example, butyl isocyanate, ifappropriate in the presence of a reaction auxiliary, such as, forexample, diazabicyclo[2.2.2]octane, and in the presence of a diluent,such as, for example, toluene, xylene or chlorobenzene, at temperaturesbetween 80° C. and 150° C. and the volatile components are distilled offunder reduced pressure after the reaction has ended (cf. the PreparationExamples).

The formula (V) provides a general definition of the heterocycles to beused as starting materials in the processes (b), (c) and (e) accordingto the invention. In the formula (V), R³⁻¹ preferably representsoptionally substituted triazolinyl of the formula below

in which Q¹ represents oxygen or sulphur and the radicals R⁴ and R⁵ eachpreferably or in particular have those meanings which have already beenmentioned above, in the description of the compounds of the formula (I)according to the invention, as being preferred or as being particularlypreferred for R⁴ and R⁵.

The starting materials of the formula (V) are known and/or can beprepared by processes known per se (cf. EP 341489, EP 422469, EP 425948,EP 431291, EP 507171, EP 534266).

The formula (VI) provides a general definition of the sulphonylchlorides to be used as starting materials in the processes (c) and (d)according to the invention for preparing the compounds of the formula(I). In the formula (VI), R¹ and R² each preferably or in particularhave that meaning which has already been mentioned above, in thedescription of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for R¹and R².

The sulphonyl chlorides of the formula (VI) have hitherto not beendisclosed in the literature; as novel substances, they also form part ofthe subject-matter of the present application and they can be preparedas described above.

The formula (VIII) provides a general definition of the(thio)carboxamides to be used as starting materials in the process (d)according to the invention for preparing the compounds of the formula(I). In the formula (VIII), Q and R³ each preferably or in particularhave that meaning which has already been mentioned above, in thedescription of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for Qand R³.

The starting materials of the formula (VIII) are known and/or can beprepared by processes known per se (cf. EP 459244).

The formula (IX) provides a general definition of thesulphonylamino-(thio)carbonyl compounds to be used as starting materialsin the process (e) according to the invention for preparing thecompounds of the formula (I). In the formula (IX), Q, R¹ and R² eachpreferably or in particular has that meaning which has already beenmentioned above, in the description of the compounds of the formula (I)according to the invention, as being preferred or as being particularlypreferred for Q, R¹ and R²; Z preferably represents fluorine, chlorine,bromine, C₁-C₄-alkoxy, phenoxy or benzyloxy, in particular representschlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (IX) are known and/or can beprepared by processes known per se.

The processes (a), (b), (c), (d) and (e) according to the invention forpreparing the novel compounds of the formula (I) are preferably carriedout using diluents. Suitable diluents are virtually all inert organicsolvents. These preferably include aliphatic and aromatic, optionallyhalogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane,petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylenechloride, ethylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether anddibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,tetrahydrofuran and dioxane; ketones such as acetone, methyl ethylketone, methyl isopropyl ketone and methyl isobutyl ketone; esters suchas methyl acetate and ethyl acetate; nitriles such as, for example,acetonitrile and propionitrile; amides such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

Suitable reaction auxiliaries or acid acceptors for use in the processes(a), (b), (c), (d) and (e) according to the invention are all acidbinders which can conventionally be used for such reactions. Preferenceis given to alkali metal hydroxides such as, for example, sodiumhydroxide and potassium hydroxide, alkaline earth metal hydroxides suchas, for example, calcium hydroxide, alkali metal carbonates andalkoxides such as sodium carbonate and potassium carbonate, sodiumtert-butoxide and potassium tert-butoxide, furthermore basic nitrogencompounds, such as trimethylamine, triethylamine, tripropylamine,tributylamine, diisobutylamine, dicyclohexylamine,ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethyl-benzylamine,N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and5-ethyl-2-methylpyridine, 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN),1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and1,4-diazabicyclo-[2,2,2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c), (d) and (e)according to the invention can be varied within a relatively wide range.In general, the processes are carried out at temperatures between −20°C. and +150° C., preferably at temperatures between 0° C. and +100° C.

The processes (a), (b), (c), (d) and (e) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to operate under elevated or reduced pressure.

For carrying out the processes (a), (b), (c), (d) and (e) according tothe invention, the starting materials which are required in each caseare generally employed in approximately equimolar amounts. However, itis also possible to employ a relatively large excess of one of thecomponents used in each case. The reactions are generally carried out ina suitable diluent in the presence of an acid acceptor, and the reactionmixture is stirred for a number of hours at the respective temperaturerequired. Work-up in the processes (a), (b), (c), (d) and (e) accordingto the invention is in each case carried out by customary methods (cf.the Preparation Examples).

If required, salts can be prepared from the compounds of the generalformula (I) according to the invention. Such salts are obtained in asimple manner by customary salt formation methods, for example bydissolving or dispersing a compound of the formula (I) in a suitablesolvent, such as, for example, methylene chloride, acetone, tert-butylmethyl ether or toluene, and adding a suitable base. The salts can thenbe isolated—if appropriate after prolonged stirring—by concentration orfiltration with suction.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed-killers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railwaytracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for the control of weeds inperennial crops for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective control of weeds inannual cultures.

The compounds of the formula (I) according to the invention are suitablein particular for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous crops, both pre-emergence andpost-emergence.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Suitable liquid solvents areessentially the following: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifying and/or foam-forming agents are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as protein hydrolysates; suitable dispersing agents are: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For the control of weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

Possible components for the mixtures are known herbicides, for example

acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, asulam,atrazine, azimsulfuron, benazolin, benfuresate, bensulfuron(-methyl),bentazon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox,bromobutide, bromofenoxim, bromoxynil, butachlor, butylate, cafenstrole,carbetamide, chlomethoxyfen, chloramben, chloridazon,chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron,cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone,clopyralid, clopyrasulfuron, cloransulam(-methyl), cumyluron, cyanazine,cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB,2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), difenzoquat,diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dinitramine, diphenamid, diquat, dithiopyr, diuron,dymron, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl),ethofumesate, ethoxyfen, etobenzanid, fenoxaprop(-ethyl),flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, fluazifop(-butyl), flumetsulam, flumiclorac(-pentyl),flumioxazin, flumipropyn, fluometuron, fluorochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurenol, fluridone,fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate(-ammonium),glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl),hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapyr,imazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin,isoproturon, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil,linuron, MCPA, MCPP, mefenacet, metamitron, metazachlor,methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam,metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron,naproanilide, napropamide, neburon, nicosulfuron, norflurazon,orbencarb, oryzalin, oxadiazon, oxyfluorfen, paraquat, pendimethalin,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propyzamide,prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron(-ethyl),pyrazoxyfen, pyributicarb, pyridate, pyrithiobac(-sodium), quinchlorac,quinmerac, quizalofop(-ethyl), quizalofop(-p-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine,terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin,thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim,triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane,trifluralin and triflusulfuron.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

(Process (a))

1.3 g (6.8 mmol) of 2,4-dimethyl-thiophene-3-sulphonamide and 1.1 g (7mmol) of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) are addedsuccessively to a solution of 1.6 g (6.4 mmol) of5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-onein 30 ml of acetonitrile. The reaction mixture is stirred at roomtemperature (about 20° C.) for approximately 15 hours and subsequentlyconcentrated under waterpump vacuum. The residue is then taken up inmethylene chloride and washed with 1N hydrochloric acid and then withwater. The organic phase is dried with magnesium sulphate and filtered.The filtrate is concentrated under waterpump vacuum and the residue isrecrystallized from isopropanol.

This gives 1.1 g (50% of theory) of5-ethoxy-4-methyl-2-(2,4-dimethyl-thien-3-yl-sulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 158° C.

Example 2

(Process (d))

At 20° C. to at most 35° C., 2.0 g (36 mmol) of potassium hydroxidepowder are added to a solution of 1.52 g (12.0 mmol) of5-methyl-1,2,4-oxadiazol-3-carboxamide in 150 ml of dioxane. After 30minutes, approximately 50 ml of dioxane are distilled off at from 30° C.to 35° C. under waterpump vacuum. The mixture is subsequently admixed alittle at a time with 2.65 g (12.6 mmol) of2,4-dimethylthiophene-3-sulphonyl chloride and the reaction mixture isstirred at room temperature (about 20° C.) for approximately 12 hours.The mixture is subsequently concentrated under waterpump vacuum and theresidue is taken up in water and acidified with 2N hydrochloric acid.The mixture is then extracted twice with 100 ml of methylene chlorideeach time. The combined organic solutions are washed with water, driedwith magnesium sulphate and filtered. The filtrate is concentrated underwaterpump vacuum and the residue is recrystallized from ethanol.

This gives 0.7 g (19% of theory) ofN-(2,4-dimethyl-thien-3-yl-sulphonyl)-5-methyl-1,2,4-oxadiazol-3-carboxamideof melting point 164° C.

By the methods of Examples 1 and 2, and in accordance with the generaldescription of the preparation processes according to the invention, itis also possible to prepare, for example, the compounds of the formula(I) listed in Table 1 below.

TABLE 1 Examples of compounds of the formula (I) Melt- ing Ex. point No.Q R¹ R² R³ (° C.) 3 O CH₃ CH₃

152 4 O CH₃ CH₃

179 5 O CH₃ CH₃

120 6 O CH₃ CH₃

137 7 O CH₃ CH₃

122 8 O CH₃ CH₃

107 9 O CH₃ CH₃

63 10 O CH₃ CH₃

130 11 O CH₃ CH₃

96 12 O CH₃ CH₃

82 13 O CH₃ CH₃

129 14 O CH₃ CH₃

117 15 O CH₃ CH₃

159 16 S CH₃ CH₃

124 17 O CH₃ CH₃

91 18 O CH₃ CH₃

128 19 O CH₃ CH₃

70 20 O CH₃ CH₃

55 21 O CH₃ CH₃

114 22 O CH₃ CH₃

163 23 O CH₃ CH₃

95 24 O CH₃ CH₃

129 25 O CH₃ CH₃

177 26 O CH₃ CH₃

165 27 O CH₃ CH₃

160 28 O CH₃ CH₃

62 29 O CH₃ CH₃

164 30 O CH₃ CH₃

125 31 O CH₃ CH₃

74 32 O CH₃ CH₃

158 33 S CH₃ CH₃

112 34 S CH₃ CH₃

147 35 S CH₃ CH₃

139 36 S CH₃ CH₃

136 37 S CH₃ CH₃

78 38 S CH₃ CH₃

97 39 O CH₃ CH₃

66 40 O CH₃ OCH₃

41 O CH₃ OCH₃

42 O CH₃ OCH₃

43 O CH₃ OCH₃

Starting Materials of the Formula (II):

Example (II-1)

A mixture of 6.0 g (29 mmol) of 2,4-dimethyl-thiophene-3-sulphonylchloride and 30 ml of 25% strength aqueous ammonia solution is stirredat room temperature (about 20° C.) for 12 hours. The resultingcrystalline product is then isolated by filtration with suction.

This gives 4.3 g (80% of theory) of2,4-dimethyl-thiophene-3-sulphonamide of melting point 135° C.

Starting Materials of the Formula (IV):

Example (IV-1)

A mixture of 19.1 g (100 mmol) of 2,4-dimethyl-thiophene-3-sulphonamide,10.0 g (100 mmol) of butyl isocyanate and 100 ml of chloroform is heatedto the boil, and phosgene is introduced into the mixture at refluxtemperature for 4 hours. The mixture is subsequently concentrated underwaterpump vacuum and the residue is subjected to distillation underoilpump vacuum.

This gives 10.3 g (47% of theory) of 2,4-dimethyl-thien-3-yl-sulphonylisocyanate of a boiling range of from 135° C. to 140° C. (at 1 mbar).

Starting Materials of the Formula (VI):

Example (VI-1)

A solution of 13.9 g (109 mmol) of 3-amino-2,4-dimethyl-thiophene in 30ml of 10% strength hydrochloric acid is cooled to 0° C. and admixed with50 ml of conc. hydrochloric acid. With cooling to from 0° C. to −5° C.,a solution of 8.6 g (125 mmol) of sodium nitrite in 22 ml of water isthen added dropwise with stirring. The reaction mixture is stirred atfrom 0° C. to −5° C. for approximately one hour. Excess sodium nitriteis subsequently destroyed using amidosulphonic acid. The resultingdiazonium salt solution is added dropwise, at about 15° C., to asolution of 12 g of sulphur dioxide in 100 ml of 1,2-dichloro-ethane.600 mg of copper(I) chloride and 600 mg of dodecyl-trimethylammoniumbromide are then added and the reaction mixture is stirred at about 40°C. for approximately one hour and at room temperature (about 20° C.) fora further 12 hours. After addition of 6 g of 30% strength hydrogenperoxide solution, the mixture is stirred for a further 30 minutes. Theorganic phase is then separated off, washed twice with water, dried withmagnesium sulphate and filtered. The filtrate is concentrated underwaterpump vacuum, the residue is digested with petroleum ether and theresulting crystalline product is isolated by filtration with suction.

This gives 9.6 g (42% of theory) of 2,4-dimethyl-thiophene-3-sulphonylchloride of melting point 79° C.

In each case by the methods of Examples (II-1), (IV-1) and (VI-1) it isalso possible to prepare, for example, the compounds of the formulae(II), (IV) and (VI) listed in Table 2 below:

TABLE 2 Examples of the compounds of the formulae (II), (IV) and (VI)[i.e. the radicals R¹ and R² apply to each of these 3 formulae]; Q is Oor S. Example No. II- IV- VI- R¹ R² 2 CH₃ C₂H₅ 3 CH₃ C₃H₇-n 4 CH₃ C₃H₇-i5 CH₃ CF₃ 6 CH₃ Cl 7 CH₃ OCH₃ 8 CH₃ OC₂H₅ 9 CH₃ OC₃H₇-n 10 CH₃ OC₃H7-i11 C₂H₅ CH₃ 12 C₃H₇-n CH₃ 13 C₃H₇-i CH₃

USE EXAMPLES Example A

Pre-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is watered with the preparation of the active compound.Advantageously, the amount of water per unit area is kept constant. Theactive compound concentration in the preparation is not important, onlythe active compound application rate per unit area is critical.

After three weeks, the degree of damage to the plants is rated in %damage in comparison with the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, for example, the compounds of Preparation Example 1, 3, 4,5, 11 and 12 exhibit very strong activity against weeds, and some ofthem are tolerated well by crop plants, such as, for example, maize andwheat (cf. Table A).

“ai.” (active ingredient)=active compound

TABLE A Pre-emergence test/greenhouse Applica- Active compound of tionrate Preparation Example (g of Bro- Cype- Lo- Se- Chenopo- Matri- Sola-No. ai./ha) Maize mus rus lium taria dium caria num

125 5 100 100 100 100 100 100 100 Applica- Active compound of tion ratePreparation (g of Bro- Cype- Lo- Se- Chenopo- Matri- Sola- Example No.ai./ha) Wheat mus rus lium taria dium caria num

125 0 100 95 100 100 100 100 100 Applica- Active compound of tion ratePreparation (g of Bro- Cype- Lo- Se- Chenopo- Matri- Sola- Example No.ai./ha) Wheat Maize mus rus lium taria dium caria num

125 0 0 95 95 100 100 90 90 80 Applica- Active compound of tion ratePreparation (g of Bro- Cype- Lo- Se- Chenopo- Matri- Sola- Example No.ai./ha) mus rus lium taria dium caria num

125 100 100 100 100 95 100 95 Applica- Active compound tion rate ofPreparation (g of Alope- Amaran- Example No. ai./ha) curus Abutilon thusSinapis Xanthium

250 70 90 90 95 90

250 70 90 90 95 — “ai.” (active ingredient ) = active compound

Example B

Post-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the amounts ofactive compound desired in each case are applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison with the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100% =total destruction

In this test, for example, the compounds of Preparation Examples 6, 13and 14 exhibit very strong activity against weeds, and some of them aretolerated well by crop plants, such as, for example, maize (cf. TableB).

TABLE B Post-emergence test/greenhouse Active compound Applica- ofPreparation tion rate Amaran- Example No. (g of ai/ha) Maize SetariaAbutilon thus Sinapis

250 10 80 — 90 100

250 — 80 80 100 100

250 10 90 — 95 95

What is claimed is:
 1. A compound of the Formula (XX)

wherein R¹ is selected from the group consisting of cyano; halogen;alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in eachcase up to 6 carbon atoms; and cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy oralkinyloxy having in each case up to 6 carbon atoms; R² is selected fromthe group consisting of cyano; halogen; alkyl, alkenyl, alkinyl, alkoxy,alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms; andcyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl,alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbonatoms; and R¹⁰ is —NH₂.
 2. The compound of claim 1, wherein R¹ isselected from the group consisting of cyano; halogen; C₁-C₄-alkyl;C₂-C₄-alkenyl; C₂-C₄-alkinyl; C₁-C₄-alkoxy; C₂-C₄-alkenyloxy;C₂-C₄-alkinyloxy; cyano-, halogen- or C₁-C₄-alkoxy-substitutedC₁-C₄-alkyl; cyano- or halogen-substituted C₂-C₄-alkenyl orC₂-C₄-alkinyl; cyano-, halogen- or C₁-C₄-alkoxy-substitutedC₁-C₄-alkoxy; and cyano- or halogen-substituted C₂-C₄-alkenyloxy orC₂-C₄-alkinyloxy; and R² is selected from the group consisting of cyano;halogen; C₁-C₄-alkyl; C₂-C₄-alkenyl; C₂-C₄-alkinyl; C₁-C₄-alkoxy;C₂-C₄-alkenyloxy; C₂-C₄-alkinyloxy; cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl; cyano- or halogen-substitutedC₂-C₄-alkenyl or C₂-C₄-alkinyl; cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkoxy; and cyano- or halogen-substitutedC₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy.
 3. The compound of claim 2,wherein R¹ and R² are both methyl.